US3997541A - Lactones of the benzazaxanthene series and dye-forming components for duplication processes - Google Patents
Lactones of the benzazaxanthene series and dye-forming components for duplication processes Download PDFInfo
- Publication number
- US3997541A US3997541A US05/492,039 US49203974A US3997541A US 3997541 A US3997541 A US 3997541A US 49203974 A US49203974 A US 49203974A US 3997541 A US3997541 A US 3997541A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- alkyl
- phenyl
- benzazaxanthene
- series
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002596 lactones Chemical class 0.000 title claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 abstract description 3
- QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical class C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- -1 aliphatic radical Chemical class 0.000 description 58
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- KEGYMUNNLPTAOY-UHFFFAOYSA-N 2-[2-hydroxy-4-(2-methylanilino)benzoyl]benzoic acid Chemical compound CC1=CC=CC=C1NC(C=C1O)=CC=C1C(=O)C1=CC=CC=C1C(O)=O KEGYMUNNLPTAOY-UHFFFAOYSA-N 0.000 description 2
- QLJFYMHMQNYOGS-UHFFFAOYSA-N 2-butyl-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC)C(=O)CC2=C1 QLJFYMHMQNYOGS-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YEEJWCWASCAQBG-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[2-hydroxy-4-(2-methylanilino)benzoyl]benzoic acid Chemical compound CC1=CC=CC=C1NC(C=C1O)=CC=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O YEEJWCWASCAQBG-UHFFFAOYSA-N 0.000 description 1
- IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
- WJCUBPCYUDXXKR-UHFFFAOYSA-N 2-(2-ethoxyethyl)-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCOCC)C(=O)CC2=C1 WJCUBPCYUDXXKR-UHFFFAOYSA-N 0.000 description 1
- IAHXZWGZTKAXQE-UHFFFAOYSA-N 2-(2-phenylethyl)-4h-isoquinoline-1,3-dione Chemical compound O=C1CC2=CC=CC=C2C(=O)N1CCC1=CC=CC=C1 IAHXZWGZTKAXQE-UHFFFAOYSA-N 0.000 description 1
- VCAVXRXBRBLYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4h-isoquinoline-1,3-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2CC1=O VCAVXRXBRBLYDE-UHFFFAOYSA-N 0.000 description 1
- BLCWNIGSFBOPQU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4h-isoquinoline-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=CC=CC=C2CC1=O BLCWNIGSFBOPQU-UHFFFAOYSA-N 0.000 description 1
- BNDWPICVAMQLBB-UHFFFAOYSA-N 2-[2-hydroxy-4-(4-methylanilino)benzoyl]-4-methylbenzoic acid Chemical compound C1=CC(C)=CC=C1NC(C=C1O)=CC=C1C(=O)C1=CC(C)=CC=C1C(O)=O BNDWPICVAMQLBB-UHFFFAOYSA-N 0.000 description 1
- QPHARHZLYSVMDP-UHFFFAOYSA-N 2-[2-hydroxy-4-(4-methylanilino)benzoyl]benzoic acid Chemical compound C1=CC(C)=CC=C1NC(C=C1O)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPHARHZLYSVMDP-UHFFFAOYSA-N 0.000 description 1
- ZGHBQUZPAPTUJN-UHFFFAOYSA-N 2-[4-(2-chlorophenyl)-2-hydroxybenzoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)Cl)C=C1O ZGHBQUZPAPTUJN-UHFFFAOYSA-N 0.000 description 1
- UMNIWQDFMWRPOX-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-hydroxybenzoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1O UMNIWQDFMWRPOX-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- LIGOQVCGDBFITB-UHFFFAOYSA-N 2-cyclohexyl-4h-isoquinoline-1,3-dione Chemical compound O=C1CC2=CC=CC=C2C(=O)N1C1CCCCC1 LIGOQVCGDBFITB-UHFFFAOYSA-N 0.000 description 1
- OOFVVDJERAFCOK-UHFFFAOYSA-N 2-cyclopentyl-4h-isoquinoline-1,3-dione Chemical compound O=C1CC2=CC=CC=C2C(=O)N1C1CCCC1 OOFVVDJERAFCOK-UHFFFAOYSA-N 0.000 description 1
- DYSIHRSXCLNOFL-UHFFFAOYSA-N 2-ethyl-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC)C(=O)CC2=C1 DYSIHRSXCLNOFL-UHFFFAOYSA-N 0.000 description 1
- LMONSPPCSINGKH-UHFFFAOYSA-N 2-hexyl-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCC)C(=O)CC2=C1 LMONSPPCSINGKH-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- JNMUQWIITYQZSA-UHFFFAOYSA-N 2-methyl-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)CC2=C1 JNMUQWIITYQZSA-UHFFFAOYSA-N 0.000 description 1
- QIUJEIYANWQBLO-UHFFFAOYSA-N 2-phenyl-4h-isoquinoline-1,3-dione Chemical compound O=C1CC2=CC=CC=C2C(=O)N1C1=CC=CC=C1 QIUJEIYANWQBLO-UHFFFAOYSA-N 0.000 description 1
- VELWDNLYIQYANO-UHFFFAOYSA-N 2-propyl-4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCC)C(=O)CC2=C1 VELWDNLYIQYANO-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100035233 Furin Human genes 0.000 description 1
- 101001022148 Homo sapiens Furin Proteins 0.000 description 1
- 101001128694 Homo sapiens Neuroendocrine convertase 1 Proteins 0.000 description 1
- 101000601394 Homo sapiens Neuroendocrine convertase 2 Proteins 0.000 description 1
- 101001072067 Homo sapiens Proprotein convertase subtilisin/kexin type 4 Proteins 0.000 description 1
- 101000701936 Homo sapiens Signal peptidase complex subunit 1 Proteins 0.000 description 1
- 101000828971 Homo sapiens Signal peptidase complex subunit 3 Proteins 0.000 description 1
- 101000979222 Hydra vulgaris PC3-like endoprotease variant A Proteins 0.000 description 1
- 101000979221 Hydra vulgaris PC3-like endoprotease variant B Proteins 0.000 description 1
- 102100032132 Neuroendocrine convertase 1 Human genes 0.000 description 1
- 102100037732 Neuroendocrine convertase 2 Human genes 0.000 description 1
- 108010022052 Proprotein Convertase 5 Proteins 0.000 description 1
- 102100036371 Proprotein convertase subtilisin/kexin type 4 Human genes 0.000 description 1
- 102100036365 Proprotein convertase subtilisin/kexin type 5 Human genes 0.000 description 1
- 102100038946 Proprotein convertase subtilisin/kexin type 6 Human genes 0.000 description 1
- 101710180552 Proprotein convertase subtilisin/kexin type 6 Proteins 0.000 description 1
- 102100038950 Proprotein convertase subtilisin/kexin type 7 Human genes 0.000 description 1
- 101710180647 Proprotein convertase subtilisin/kexin type 7 Proteins 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
Definitions
- the invention relates to lactones of the benzazaxanthene series of the formula (I): ##SPC1##
- R 1 is hydrogen or alkyl of one to three carbon atoms
- R 2 is phenyl or phenyl bearing alkyl of one to three carbon atoms, chloro and/or bromo as substituents;
- R 3 is hydrogen or an unsubstituted or substituted aliphatic radical with one to twenty carbon atoms or an unsubstituted or substituted aromatic radical;
- X and Y are hydrogen, chloro, bromo, nitro or alkyl of one to three carbon atoms;
- Z is hydrogen, chloro, bromo, alkyl of one to three carbon atoms or phenyl
- n is each the integer 1 or 2.
- the invention relates particularly to lactones of the benzazaxanthone series of the formula (I) in which R 2 is phenyl or phenyl bearing alkyl of one to three carbon atoms, chloro or bromo as substituents;
- R 3 is hydrogen, phenyl, alkyl of one to six carbon atoms, phenyl-substituted alkyl of one to six carbon atoms in the alkyl, phenyl bearing alkyl of one to three carbon atoms or chloro as substituents;
- R, x, y, z, m and n have the above meanings.
- R 3 examples of unsubstituted and substituted aliphatic and aromatic radicals R 3 are: alkyl of one to 20 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, 1,4-dimethylpentyl, n-hexyl, 5-methylhexyl, 2-ethylhexyl, n-decyl, 2-methylnonyl, n-dodecyl, n-tridecyl, stearyl, cyanoalkyl and hydroxyalkyl of one to six carbon atoms such as 2-cyanoethyl, ⁇ -cyanopentyl, ⁇ -cyanohexyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-methyl-2-hydroxypropyl, 2-methyl-2-hydroxypent
- Hydrogen is preferred for R 1 .
- Phenyl which may bear alkyl of one to three carbon atoms as a single substituent is preferred for R 2 .
- Dye-forming components which have particular industrial significance are lactones of formula (I) in which R 1 , X, Y and Z are hydrogen, R 2 is phenyl, o-tolyl, p-tolyl, o-chlorophenyl or p-chlorophenyl and R 3 is alkyl of one to six carbon atoms in the alkyl radical and which may bear phenyl as substituent, phenyl, tolyl or ethylphenyl, and, among these, particularly compounds of the formula: ##SPC3##
- R 3 ' is phenyl or alkyl bearing phenyl as a substituent and of one to six carbon atoms in the alkyl radical.
- Benzazaxanthenes of formula (I) may be prepared by the condensation of a benzoylbenzoic acid of the formula (II): ##SPC4##
- R is hydrogen, lower alkyl or acyl with a homophthalimide of formula (III) ##SPC5##
- the reaction product for the purpose of processing may then be introduced in the cooled condition into a dilute aqueous solution of an alkali metal or ammonium hydroxide from which the insoluble reaction product may be separated and then obtained in the pure state for example by dissolving it and reprecipitating it or by recrystallizing it.
- the reaction product often crystallizes out from the condensation product; it may then be isolated and purified by dissolving it and reprecipitating it or by recrystallizing it.
- benzoylbenzoic acids are:
- homophthalimides are: N-methylhomophthalimide, N-ethylhomophthalimide, N-propylhomophthalimide, N-butylhomophthalimide, N-hexylhomophthalimide, N-2-phenylethylhomophthalimide, N-2-ethoxyethylhomophthalimide, N-3-(2'-phenoxyethoxy)-propylhomophthalimide, N-(2-dimethylamino)-ethylhomophthalimide, N-phenylhomophthalimide, N-p-tolyhomophthalimide, N-p-chlorophenylhomophthalimide, N-4-methoxyphenylhomophthalimide, N-cyclopentylhomophthalimide and N-cyclohexylhomophthalimide.
- the resulting lactones of formula (I) are colorless compounds. Used as such or dissolved in non-polar or weakly polar solvents such as hydrocarbons, chlorohydrocarbons, esters or ketones, they react with acid substances, with cleavage of the lactone ring, to form the corresponding deeply colored dye salts. Since this reaction is caused even by substances such as china clay, zeolites, bentonites, silica and phenolic condensation products, which are suitable for coating or incorporating into paper, the lactones of this invention are outstandingly suitable as dye-forming components for pressure-sensitive recording materials, especially for the production of copying papers.
- non-polar or weakly polar solvents such as hydrocarbons, chlorohydrocarbons, esters or ketones
- the dye-forming components according to the invention may be made into a paste which is applied to paper and the surface provided with a protective layer.
- a particularly advantageous application consists in enclosing the dye-forming component in solution in a solvent having little or no volatility, for example chloroparaffin, trichlorodiphenyl or an alkylbenzene bearing one or more substituents, within microcapsules and coating the paper with them. Under writing pressure the dyeforming component is brought into contact with an acid receptive layer so that characters appear.
- the acid component and the microcapsules may also be present in a single layer.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732338954 DE2338954A1 (de) | 1973-08-01 | 1973-08-01 | Lactone der benzazaxanthenreihe und farbbildner fuer kopierverfahren |
| DT2338954 | 1976-08-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| USB492039I5 USB492039I5 (enrdf_load_stackoverflow) | 1976-02-24 |
| US3997541A true US3997541A (en) | 1976-12-14 |
Family
ID=5888569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/492,039 Expired - Lifetime US3997541A (en) | 1973-08-01 | 1974-07-26 | Lactones of the benzazaxanthene series and dye-forming components for duplication processes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3997541A (enrdf_load_stackoverflow) |
| JP (1) | JPS5049331A (enrdf_load_stackoverflow) |
| BE (1) | BE818368R (enrdf_load_stackoverflow) |
| CH (1) | CH605961A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2338954A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2245657B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1478516A (enrdf_load_stackoverflow) |
| IT (1) | IT1048286B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4794069A (en) * | 1986-07-15 | 1988-12-27 | Shin Nisso Kako Co., Ltd. | Spirobenzanthracene phthalide compounds, processes for preparing same and color forming recording materials containing said compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787325A (en) * | 1970-11-16 | 1974-01-22 | Ncr | Alkylamino spiro {8 12-h{8 1{9 benzopyran {8 3,2f{9 {14 quinoline-12,1{40 phthalide |
-
1973
- 1973-08-01 DE DE19732338954 patent/DE2338954A1/de active Pending
-
1974
- 1974-07-26 US US05/492,039 patent/US3997541A/en not_active Expired - Lifetime
- 1974-07-29 CH CH1042574A patent/CH605961A5/xx not_active IP Right Cessation
- 1974-07-30 FR FR7426412A patent/FR2245657B2/fr not_active Expired
- 1974-07-31 GB GB33739/74A patent/GB1478516A/en not_active Expired
- 1974-07-31 IT IT52372/74A patent/IT1048286B/it active
- 1974-08-01 JP JP49087599A patent/JPS5049331A/ja active Pending
- 1974-08-01 BE BE147181A patent/BE818368R/xx active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787325A (en) * | 1970-11-16 | 1974-01-22 | Ncr | Alkylamino spiro {8 12-h{8 1{9 benzopyran {8 3,2f{9 {14 quinoline-12,1{40 phthalide |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4794069A (en) * | 1986-07-15 | 1988-12-27 | Shin Nisso Kako Co., Ltd. | Spirobenzanthracene phthalide compounds, processes for preparing same and color forming recording materials containing said compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| USB492039I5 (enrdf_load_stackoverflow) | 1976-02-24 |
| GB1478516A (en) | 1977-07-06 |
| JPS5049331A (enrdf_load_stackoverflow) | 1975-05-02 |
| FR2245657A2 (enrdf_load_stackoverflow) | 1975-04-25 |
| FR2245657B2 (enrdf_load_stackoverflow) | 1977-03-11 |
| DE2338954A1 (de) | 1975-02-20 |
| IT1048286B (it) | 1980-11-20 |
| BE818368R (fr) | 1975-02-03 |
| CH605961A5 (enrdf_load_stackoverflow) | 1978-10-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3931182A (en) | Lactones of the diazaxanthene series, their production and their use as dye-forming components for copying methods | |
| US4154463A (en) | Pressure-sensitive or heat-sensitive recording material containing a carbazolyl methane compound | |
| US3971808A (en) | Spirodipyrans and chromogenic materials for copying processes | |
| DE1795737A1 (de) | Chromogene verbindungen und ihre verwendung in druckempfindlichem aufzeichnungsmaterial | |
| DE2750283C2 (de) | Druck- und wärmeempfindliches Aufzeichnungsmaterial | |
| US3985376A (en) | Dye precursors for pressure-sensitive recording material | |
| CH628290A5 (de) | Druck- oder waermeempfindliches aufzeichnungsmaterial. | |
| US3997541A (en) | Lactones of the benzazaxanthene series and dye-forming components for duplication processes | |
| US3946017A (en) | Lactones of the benzaxanthere series and dye-forming components for use in duplication processes | |
| US4916240A (en) | Hetero-polycyclic aromatic compounds | |
| US4594601A (en) | Fluoran compounds | |
| US3137685A (en) | Aceto-acetarylide azo quinoline coloring compounds | |
| EP0180643B1 (en) | Fluoran compounds | |
| US4029677A (en) | Spirodipyrans useful as dye precursors for copying processes | |
| US4564679A (en) | Chromogenic compounds | |
| US4587538A (en) | Record material | |
| US3896128A (en) | Lactones of the diazaxanthene series and dye precursors for copying processes | |
| US4052398A (en) | Diazarhodamine-lactones, their manufacture and their use as dye intermediates for copying processes | |
| US3992450A (en) | 2,3-Disubstituted-1-indanones | |
| EP0192328B1 (en) | Chromogenic compounds | |
| US3989716A (en) | Pyrrylfluoran compounds | |
| US3974175A (en) | Nitro-chromeno pyrazole compounds their manufacture and use | |
| US3884506A (en) | Pressure-sensitive copying papers containing fluoran compounds | |
| GB2035354A (en) | Chromogenic propenylenesulfone compounds their manufacture and use | |
| FI62491C (fi) | Tryck- eller vaermekaensligt uppteckningsmaterial |